Ethyl formate → HCID 86758821, compound

HRID 1057638Notes

Reaction equation

HRID 1057638 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][NH2:24])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([CH3:25])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:26](OCC)=[O:27]>ClCCl>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][NH:24][CH:26]=[O:27])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([CH3:25])[CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8025Ethyl formate2×HCID 9911426HCID 9911426, compound

Product 1

HCID 86758821HCID 86758821, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
62 °C

Procedure

A mixture of 2-[(9-benzyl-6-methyl-9H-carbazol-4-yl)oxy]ethylamine (0.2974 g, 0.90 mmol), dichloromethane (4 mL) and ethyl formate (4 mL) is heated at 62° C. Additional dichloromethane (6 mL) and ethyl formate (6 mL) are added. After 4 h, the mixture is concentrated to dryness and the residue is chromatographed on silica gel (100 mL) using methanol/dichloromethane (4/96). The resulting solids are recrystallized from ethyl acetate/dichloromethane/hexane to give 0.2716 g (84%) of the title compound; 1H NMR (CDCl3) δ2.55, 3.94, 4.36, 5.48, 6.11, 6.64, 6.99, 7.11, 7.24, 7.32, 8.06, 8.28.

Workup

  1. concentrationthe mixture is concentrated to dryness
  2. customthe residue is chromatographed on silica gel (100 mL)
  3. customThe resulting solids are recrystallized from ethyl acetate/dichloromethane/hexane

Sources & evidence

ORD record
ord-01cc315b963e46f98dedf6da374103ad
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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